Will Middlebrooks didn’t have an especially accomplished career. Hampered by injuries, the slugging third baseman saw action in just 347 big league games — the bulk of them with the Boston Red Sox — before hanging up his spikes shortly after his 29th birthday. But there were memorable moments along the way, and he has good stories to go with them. Now a broadcast analyst for the Red Sox, Middlebrooks shared several of them in the latest installment of our Challenging Career Quiz series.
I began by asking which pitcher he faced the most times.
“I had the most success against Mark Buehrle, and it could have been him,” replied Middlebrooks, who logged 262 hits, including 43 home runs, while playing from 2012-2017. “I know I faced him a lot. Was it Buerhle?”
Nope. Middlebrooks stood in the box against the longtime Chicago White Sox southpaw 19 times, going 8-for-18 with a pair of doubles and a hit-by-pitch, but it’s another hurler who has the honor. Asking Middlebrooks if he had any other guesses prompted a good exchange.
“Can you give me a hint?”
“He owned you.”
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“A lot of pitchers owned me. Who was it?”
I let him know that the answer is Chris Tillman.
“Oh, OK. He was nasty those years,” Middlebrooks said of the erstwhile Baltimore Orioles ace, against whom he went 1-for-20 with five strikeouts and a walk. “That is when he was throwing super sinkers, big time two-seamers. I don’t think there is a stat for this, but he probably broke more of my bats than anyone else’s. He had great movement, and wasn’t afraid to pitch in. Even when he would throw a ball that started in the middle of the plate, you would think, ‘OK, this is one I can do something with,’ and it would still get off the plate, and off the barrel. It would hit the label and split your bat.”
The most hits Middlebrooks recorded against a pitcher is a two-way tie between Buehrle and a Taiwanese left-hander whose name he couldn’t come up with. Also an Oriole (and later a Miami Marlin), Wei-Yin Chen surrendered eight hits in 19 at-bats in his matchups against the righty swinger. Upon learning who it was, Middlebrooks shared one of his stellar stories.
“I debuted March 2, 2012 against Oakland,” he recalled. “We had an off day the very next day, and then Baltimore came in after that. I faced Chen in my second game in the big leagues, and the reason that stands out is Dustin Pedroia. He told me things about Fenway Park right after I got here, and one of them is that fly balls down the left field line, even if they look like they’re going to go five or six rows into the stands, sometimes hit off the wall and come back toward the field.”
“Chen threw me a changeup down and in, and I hit it in the air to left,” continued Middlebrooks. “I thought it was going out and didn’t run out of the box. Then I looked up and saw that it was coming back, and ended up just getting a single out of it. Pedroia ripped me to shreds. He was yelling at me from the dugout, giving me the business. When I got back to the dugout, he really let me have it. Never again did I hit a ball even remotely close to that and not run hard out of the box.”
Middlebrooks didn’t take either of Chen or Buehrle deep, although he did record a pair of doubles against both. I asked him why he had so much success against the more accomplished of the two.
“I saw lefties pretty well,” Middlebrooks replied. “He didn’t overwhelm you with velocity at that point. He’d never been a big velocity guy, and in his last couple years in the league, when he was in Toronto, he was in the truest sense ‘a pitcher.’ He would use his movement and deception, his changeup, pitch in and out. But I never had to worry about getting beat by a fastball, so I just stayed in there, over the plate, a little more than I did against many guys.
“Something else I would do against him was use Mike Napoli’s bats. They were big, they were heavier, and they slowed me down. It was easy to be early on Buehrle, with his slower velocity — his changeup was in the 70s — so that big bat, this 35-inch, 34-ounce telephone pole, would help slow my bat down to stay on his stuff.”
What about the pitcher who fanned him the most times?
“It would have to be Jeremy Hellickson,” responded Middlebrooks, nailing the correct answer with little hesitation. “He had the changeup from hell. The Tampa Bay Rays had Hellickson, James Shields, eventually Chris Archer, and they started this trend of right-on-right changeups. It really wasn’t popular in baseball at the time, because pitchers wanted the changeup to move away from the batter, but they really got after that.
“Hellickson had a straight change. Out of his hand, it looked the same as his four-seam fastball. It didn’t have side spin like James Shields’ where you could pick it up out of hand, even though it was really good with his arm action. Hellickson was straight over the top, he had a good four-seamer, and then his changeup would have that four-seam rotation but be a lot slower. I think he could have literally stood on the mound and told me it was coming, and still corkscrewed me into the ground. It was like he had a parachute on the back of it.”
Middlebrooks went 2-for-17 against Hellickson with 10 strikeouts and nary a walk. As for the pitcher who issued him the most free passes, he had no idea. The answer was Archer, with just four.
“If you threw the rosin bag over the plate, I was probably going to hack at it,” admitted the former free-swinger, who had a 5.2% career walk rate. “But Archer… I wouldn’t have guessed that. Good velocity. When he came up, he was upper 90s, and in the 2010s anything over 95 from a starter was pretty special. He had a good arm. And his slider was filthy, although he didn’t throw it for strikes a lot. Any time you saw a slider out of his hand, it was an auto-take. I got a lot of sliders from righties, because I was a fastball hitter, and was able to lay off that pitch from him.”
Naming the two pitchers he went yard against the most times wasn’t a challenge.
“Roy Oswalt and R.A. Dickey,” the Texarkana, Texas native stated. “I got them both twice. Dickey was the first two of a three-homer game I had in Toronto. The third one was actually off of Dave Bush, who was our pitching coach when I started here as an analyst. So that was pretty cool.”
The dingers he hit off Dickey weren’t on knuckleballs.
“He was tipping his fastball,” recalled Middlebrooks. “He was coming off of a Cy Young the year before, in 2012, and this would have been on April 7, 2013. I remember that because it was one of the best games of my career: 4-for-5 with a double and three home runs. In my last at-bat, I crushed the ball, but got jammed just enough that it was caught at the wall; I almost got a fourth one. But yeah, he was tipping his fastball. He would do this thing where he would come set and kind of wiggle his glove, and he wiggled it just a little more on his fastball. And his fastball was 86-88, a little two-seamer. I hit the double off a knuckleball — it was right over the third base bag — and then my two home runs were on fastballs. One was to right, and the other was a moonshot up in the second deck by the Budweiser sign, just to the left of center field by the restaurant.”
“Oswalt is a cool story,” Middlebrooks went on to say. “My rookie year was 2012, and he was with Texas and toward the end of his career. He had been around forever, and was a legend. I grew up in Texas, so I remember watching him a ton with Houston. I pinch-hit against him and hit a home run just over the Green Monster. It got reviewed, because it hit at the very top of the wall. I remember standing in the dugout, waiting, waiting, while they reviewed it.
“The second home run was in Colorado, late in the 2013 season. It was the only other time I faced him — I was 2-for-2 against Oswalt — and it was actually the game where Todd Helton hit the last home run of his career. Jake Peavy was on the mound, and Jake was almost honored that he gave up the last one [hit] by Helton. But I had started that game 0-for-3 with a couple of strikeouts, and it was one of those days where everyone was hitting except for me. It was kind of, ‘What are we doing? We’re scoring a lot of runs, and I can’t even get hit.’ They bring a righty in — his name was [Rob] Scahill — and I hit a three-run homer in my fourth at-bat. I’m thinking, ‘OK, that’s a day saver.’ Then I ended up getting another at-bat in the top of the ninth. Oswalt is pitching, the bases are loaded, and he throws me one of those slow, 60-something-mph curveballs that he would mix in. I leaned out and kind of one-handed it down the line. It was one of those Coors Field homers. I had started the game 0-for-3 with two strikeouts, then ended it 2-for-5 with two homers and seven RBIs. It was the most baseball thing ever.”